Northwest Chicago Beach Vacations

Book a Beach Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to ¥109,000 when you book a flight and hotel together*
  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
  • Rest easy

    Plan, book, and manage your trip all in one place

Top Beach vacation packages in Northwest Chicago

Price found within the past 48 hours. Click for updated prices.
Level Chicago - River North

Level Chicago - River North

Downtown Chicago
¥265,422
per person
Sep 26 - Sep 29
found 6 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (1,043 reviews)
Highlights Loved everything about this space! Just look at this breathtaking view. Photos and videos can’t even come close to the real thing. Washer and dryer, fully functional kitchen with nespresso maker, beautiful bathrooms, super comfortable beds, impressively quiet, and the balcony! Perfect location for walking (or short uber ride) to everything. Rooftop pool and hot tub were amazing. Rooms The rooms were massive, beds were so comfortable, and had everything we needed. Location It’s in a perfect location for walking and enjoying the city, without being over crowded. Parking The parking was the only struggled; you have to call and hope someone at the front desk will answer to let you into the garage. It took several calls and walking back into the lobby to get access. Can improve We also didn’t get our free bottle of wine that was promoted on the Expedia listing. There were a lot of spiders on the balcony, but they were harmless web spinners. Amenities The rooftop pool and hot tub added an extra layer of fun to the experience. We didn’t get a chance to experience the arcade, but that was a cool amenity. Noise level Super quiet. The staff Super impressed with the staff, who read my note about this being a special trip, and then giving us a room that exceeding our expectations.

Reviewed on Aug 14, 2026

Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

Downtown Chicago
¥360,399
per person
Sep 18 - Sep 24
found 17 hours ago
Roundtrip non-stop flight included
Fukuoka (FUK) to Chicago (ORD)
8.2/10 Very Good! (2,899 reviews)
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

Downtown Chicago
¥539,890
per person
Sep 18 - Sep 24
found 17 hours ago
Roundtrip non-stop flight included
Fukuoka (FUK) to Chicago (ORD)
9.6/10 Exceptional! (1,960 reviews)
LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

Downtown Chicago
¥442,398
per person
Sep 18 - Sep 24
found 17 hours ago
Roundtrip non-stop flight included
Fukuoka (FUK) to Chicago (ORD)
9.4/10 Exceptional! (3,808 reviews)
The entire property and all staff exceeded my expectations!

Reviewed on Aug 14, 2026

Swissotel - Chicago

Swissotel - Chicago

Downtown Chicago
¥273,911
per person
Sep 26 - Sep 29
found 6 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9/10 Wonderful! (3,537 reviews)
Best hotel service in Chicago

Reviewed on Aug 14, 2026

Don't see what you're looking for?
See all available trips from Tokyo to Northwest Chicago
View all trips

5* Beach vacations in Northwest Chicago

Price found within the past 48 hours. Click for updated prices.
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

Downtown Chicago
¥539,890
per person
Sep 18 - Sep 24
found 17 hours ago
Roundtrip non-stop flight included
Fukuoka (FUK) to Chicago (ORD)
9.6/10 Exceptional! (1,960 reviews)
The Peninsula Chicago

The Peninsula Chicago

Downtown Chicago
¥764,728
per person
Sep 18 - Sep 24
found 17 hours ago
Roundtrip non-stop flight included
Fukuoka (FUK) to Chicago (ORD)
9.8/10 Exceptional! (1,003 reviews)
Incredible hotel. Truly what all hotels should aspire to be. Not one bad experience while there. This hotel is phenomenal.

Reviewed on Aug 13, 2026

Don't see what you're looking for?
See all available trips from Fukuoka to Northwest Chicago
View all trips

3 Night Beach vacations in Northwest Chicago

Price found within the past 48 hours. Click for updated prices.
The Allegro Royal Sonesta Hotel Chicago Loop

The Allegro Royal Sonesta Hotel Chicago Loop

Downtown Chicago
¥255,013
per person
Sep 26 - Sep 29
found 6 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9/10 Wonderful! (2,720 reviews)
Swissotel - Chicago

Swissotel - Chicago

Downtown Chicago
¥273,911
per person
Sep 26 - Sep 29
found 6 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9/10 Wonderful! (3,537 reviews)
Best hotel service in Chicago

Reviewed on Aug 14, 2026

Level Chicago - River North

Level Chicago - River North

Downtown Chicago
¥265,422
per person
Sep 26 - Sep 29
found 6 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (1,043 reviews)
Highlights Loved everything about this space! Just look at this breathtaking view. Photos and videos can’t even come close to the real thing. Washer and dryer, fully functional kitchen with nespresso maker, beautiful bathrooms, super comfortable beds, impressively quiet, and the balcony! Perfect location for walking (or short uber ride) to everything. Rooftop pool and hot tub were amazing. Rooms The rooms were massive, beds were so comfortable, and had everything we needed. Location It’s in a perfect location for walking and enjoying the city, without being over crowded. Parking The parking was the only struggled; you have to call and hope someone at the front desk will answer to let you into the garage. It took several calls and walking back into the lobby to get access. Can improve We also didn’t get our free bottle of wine that was promoted on the Expedia listing. There were a lot of spiders on the balcony, but they were harmless web spinners. Amenities The rooftop pool and hot tub added an extra layer of fun to the experience. We didn’t get a chance to experience the arcade, but that was a cool amenity. Noise level Super quiet. The staff Super impressed with the staff, who read my note about this being a special trip, and then giving us a room that exceeding our expectations.

Reviewed on Aug 14, 2026

Don't see what you're looking for?
See all available trips from Tokyo to Northwest Chicago
View all trips

Things to do

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

¥4,309
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Chicago: Willis Tower Skydeck and The Ledge Ticket

Chicago: Willis Tower Skydeck and The Ledge Ticket

¥7,518
per adult
88% of travellers recommend
Chicago: Willis Tower Skydeck and The Ledge Ticket
Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

Chicago: Navy Pier Centennial Wheel Ticket

¥3,920
per adult
90% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
See all activities in Northwest Chicago
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.